How to Pick a Derby Winner

In search of the next California Chrome? These tips will help you pull away from the pack.

Every great race is a great story. Even when the favored horse has an experienced jockey and an ace team. The thing not to do is think you “know” a good horse. If you wanna have fun at a horse race and lose money, buy a round of juleps. If you want to place a serious bet, don’t just go with whatever cutesy name strikes your fancy.

Since it is such a similar endeavor to picking a stock, make some picks before you make any real bets. Then watch. The fastest horse once clocked in at 55 mph. That’s 5 mph behind the cheetah. So the worst that can happen is you get to watch a human being ride one of the world’s fastest animals.

The best that can happen is your horse comes in, you win big and end up throwing back juleps with the cutest lass in the winner’s circle. Here are a few ways to boost those chances.

American Pharoah, Materiality, El Kabeir, Upstart and Far Right all have run big races on off-tracks. (Read: mud.) In your mind, their odds should go up if the track is wet.

1. Check the oddsThe man to follow is Daily Racing Forum National Handicapper and the only guy in the Derby with a cooler name than the horses: Mike Watchmaker. Check out Watchmaker’s Odds which have already put the favorite horse American Pharoah in the lead. Watchmaker’s super-insider-y, trash-talkin’ Twitter feed is a blast. Unsurprising, American Pharoah has the best odds (7-2).

2. Study the final workoutsIn this case, American Pharoah has a final workout of 58:62. When a horserace can be won literally by a nose the 00:00s matter. This is a good measure of how ready a horse is to race. But does not factor in how the jockeys or horses will interact.

3. Keep an eye on the weatherAmerican Pharoah, Materiality, El Kabeir, Upstart and Far Right all have run big races on off-tracks. (Read: mud.) In your mind, their odds should go up if the track is wet.

4. Consider the long shotsNo sporting competition is any fun when the genetically destined athlete with the most training and money wins. So keep your eyes on Stanford (30-1 odds). Materiality (12-1) crushed Stanford in their last race, but Stanford had a stronger workout (1:01:06) and Materiality (workout: 1:01:08) is not as experienced. Stanford has a “pacesetter” running style, meaning that he has yet to flash the finishing kick needed to win a big race.

5. Pick a coupleThis makes the Derby great. But it’s a waste of money unless there are 20 horses in the field. If you feel really strongly about which horse will come in first and second, ask for an Exacta at the window. If you think you can just pick the top two in any order, ask for an Exacta Box. But say you like Toyota Blue Grass Stakes winner Carpe Diem (7-1) and Firing Line (18-1). Don’t put $20 on either, put $14 to win on Carpe Diem and $6 to win on Firing Line and you could net $112 or $114 if one or the other triumphs.

6. Get to the track early and listenThe best race of my life came down to a NAFTA-ish immigration law. A foreign jockey can’t ride an American-owned horse, and vice versa. So one day at Belmont a foreign-owned horse was missing a jockey. Any old guy from the stable can’t just hop on. Soon we heard that the jockey to watch had opted to hit the track on a losing horse earlier in the day. By then the odds were set, training intervals were in. None of their data changed, but the weather had turned, and that jockey was ready.

I was with the owners of his horse and, knowing they would probably take me out to dinner either way, I dropped $100 on an Exacta box. That was a great, great day.